One Log Cabin and 800 Yoga Mats: Some Unconventional Tax Deductions from My Life in 2014


My tax return is complicated for a lot of reasons. First, I run several different businesses which all have their own set of accounting. WDS, our annual gathering, has its own legal structure, including a foundation that is completely separate from all my other projects. Last year we started an all-new event that also has its own legal structure.

So yeah, it’s complicated. It takes about 20 hours just to prepare all the info for my accountant, and as with most tax-prep tasks, it’s not usually a fun process. But I do enjoy seeing some of the charges on my statements from the previous year. They remind me of the crazy life I have, and the many fun experiences that I’m fortunate to participate in.


– 800 custom-branded yoga mats

In 2014, we set a Guinness World Record on Pioneer Courthouse Square in downtown Portland, Oregon. Making this happen required a herculean effort—from our Adventure Czar, our production team, many, many volunteers, and 800+ participants.

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It also required 800+ custom-branded mats, which we purchased in bulk and then screen-printed at a local shop. (And for everyone who’s asked, no, we don’t have any extra. We used 100% of them for the event. But yes, there will be another world record attempt this year — you should join us!)

Cost: $7,483

– One legit log cabin, interior-only

After announcing our new event, Pioneer Nation, we decided to have some fun with the set. There was only one real choice: naturally, an event focused on the modern-day Oregon Trail would have a legit log cabin.

You can’t just go to Ikea and pick up a ready-to-assemble log cabin (we tried). We commissioned it from the same local craftsman we’ve used for WDS installations, and as you can see—it was pretty awesome.

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Uh, just one problem: where to put it after the event is over? Yeah. I really should have thought about that.

Cost: $4,100

– The best bathroom sign ever (and lots of other signs)

We spent thousands (and thousands) of dollars on signage for the two events. It sounds crazy, but we need way-finding signs, banners, wall signs, and just all kinds of “here’s where stuff is” signs.

My favorite, though, is now installed in my guest bathroom.

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Cost: $17,216

– Scholarships for Real Life: Initial Grants

After WDS 2013 (i.e. two WDS’s ago), we established a foundation to provide microgrants for people doing interesting work that doesn’t usually qualify for other funding.

Our initial grantees were:


We’ll have some updates on these projects soon, and—just as exciting—a new round of applications for this year’s awards.

Cost: $60,000

– One dream machine

For last year’s WDS, we had a special sendoff—but before we could have the sendoff, we had to select a few special people. To do that, we created a “Dream Machine” (AKA video booth) that would whisk attendees into the future and ask them what their life was like five years into the future.


The video below tells what happened next, from the perspective of one of the attendees who was selected.

Cost: hard to estimate. The physical costs for the Dream Machine were around $2,000, but producing the whole project was approximately $10,000.

– Whole bunch of wooden nickels

At this year’s event, we ordered some special tokens that could be used in place of drink tickets (so boring!) at the Portland Experience, an afternoon at the park blocks that featured dozens of vendors and showed off our city to all the visitors.


(Side note: We ordered these from, which is obviously not an affiliate link. Wooden Nickel, Inc. has been around since 1945, and it looks like their website has, too.)

Cost: $1,824

– Web hosting and internet services for far too many sites

I have a huge category in my tax return for “Internet Services,” which consists of everything from web hosting to internet access (at home, at my office, on the go, GoGo, paid internet elsewhere, etc.).

We also use a ton of different services for managing newsletters and all kinds of other stuff that I don’t understand, at least for the technical side. But it’s important!


Cost: $28,000+ (no joke!)

– Lots of pizza

When I say a lot, I mean a lot. I love the old story of Mailchimp determining their company’s growth by the number of pizzas required per meeting.


Over at World Domination HQ, we don’t have pizza for every meeting—sometimes our resident Voice of Reason will make a nice crockpot of delicious soup (always vegan and gluten-free). But pizza is a go-to when I’m in charge of catering, so we tend to order a lot of it.

Cost: $1,823

– Lots of travel

For many years, travel has always been my greatest business and personal expense. I’ve gladly chosen to make travel a priority, choosing it instead of buying a car (at least for many years), going into debt for more higher education, and really ahead of just about anything else. If I had to cut costs, travel would be the last thing I’d cut.


Last year I went to fewer places than usual, but I still went a lot of places, relatively speaking. (In the 2014 Annual Review I published a full list.) Of particular interest for the tax return was my 40-city book tour, most of which is a strict business expense as I was doing nothing but meeting with readers and talking about the book during the entire time.

Cost: a bajillion dollars. Well, that’s not quite the precise number, but it was a lot. And it was all worth it and I’d do it all again.


I’m actually pretty conservative in my tax return. I don’t write off travel that isn’t specifically for “business,” even though my “business” is 100% integrated with my life. I don’t deduct clothing purchases or haircuts, even though supposedly public speakers can do that. (My haircuts cost $12 each, so I’m not too worried about it.)

No one likes paying taxes, but I’m grateful for the chance to do interesting work.

Will you have any fun or interesting deductions this year?

Comments here.


Images: Don, Woodley, Gunes, Jason

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  • Chris Remus says:

    Hi Chris! The $100 Startup inspired me to write Tax Pain Relief to help take the pain out of taxes, tackling many of the challenges you write about here. I’d love for you to try it out and see if Tax Pain Relief can give you some of those 20 hours back!

    Before developing Tax Pain Relief, I was in a similar, albeit smaller ;), boat, as taxes were taking me at least 20-24 anxiety-filled hours each year to file. This past April, with Tax Pain Relief in place, it took me less than 30 minutes to get everything over to my accountant that he needed, while I was on my way out the door to catch a flight to the Dominican Republic, for a long overdue vacation. That’s when I decided to document the process, hoping to share the relief that I experienced, with as many people as possible.

    Thanks again for the inspiration!

  • Chris Guillebeau says:

    Thanks, Chris – congrats on the new service. Not sure that my 20 hours could be reduced by much, but helping people simplify their process is certainly a big need.

  • Mike Goncalves says:

    Haha! Loved this post Chris and all the expenses you shared with us. I’m sure your accountant is use to it by now but I’d still like to see the look on their face when they see some of your receipts like 800 yoga mats, and indoor cabin,. and LOTS of pizza….awesome! And I thought my expenses of $500 for hosting and internet services was expensive….28K? Holy cow! Good stuff man, thanks for sharing and all you do – cheers!

  • Heather Furby says:

    I love this…it’s seeing the money-making creative side of business (and darn it, it still costs money!). We launched Camp CAS (Cause and Success) and a Female Founders Camp – bringing back summer camp for movers, shakers and business rule breakers! So…I also got a tax deduction for…3 goats. Yep. Miniature Nigerian Dwarf goats. It’s part of our brand…and one of them, Dave, is about to launch his own FB page. He’s quite the entrepreneurial goat…

  • Joel says:

    I would have guessed closer to “one gazillion” when it came to the travel category :).

    I’m curious how many domains you own now 🙂

  • J Sterzinger says:

    More of a reflection moment doing my taxes this year. That was when I deducted my shots needed when I went to China, because that was my first stamp of my passport partaking in the organization International Habitat for Humanity, building a house. Unreal !!!

  • Jessica says:

    Awesome post, thanks for sharing Chris! The 800 Yoga Mats part really caught my attention. My first reaction was “okay, where can I get one?” but read on and found the answer haha. I’m really looking forward to WDS2015 though…it’ll be my first one!

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